POLAR CONTROL OF THE REGIOSELECTIVITY OF HETARYNE CYCLOADDITIONS - SYNTHESIS OF ELLIPTICINE

Authors
DIAZ MT COBAS A GUITIAN E CASTEDO L
Citation
Mt. Diaz et al., POLAR CONTROL OF THE REGIOSELECTIVITY OF HETARYNE CYCLOADDITIONS - SYNTHESIS OF ELLIPTICINE, Synlett, (2), 1998, pp. 157
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
2
Year of publication
1998
Database
ISI
SICI code
0936-5214(1998):2<157:PCOTRO>2.0.ZU;2-6
Abstract
A regioselective cycloaddition between 3-dimethyl-4-(phenylsulfonyl)-4 H-furo[3,4-b]indole and 2-chloro-3,4-didehydropyridine is the key step of a modification of Gribble's approach to ellipticines. The use of a fluoride-promoted elimination for the generation of the pyridyne and the control of the regioselectivity of the cycloaddition improve the y ield of ellipticine by a factor of 3.